MX2007007345A - Compuestos heterociclicos novedosos utiles para el tratamiento de trastornos inflamatorios y alergicos. - Google Patents

Compuestos heterociclicos novedosos utiles para el tratamiento de trastornos inflamatorios y alergicos.

Info

Publication number: MX2007007345A
Authority: MX; Mexico
Prior art keywords: formula; substituted; unsubstituted; methoxy; furo
Prior art date: 2004-12-17

Application number

MX2007007345A

Other languages

English (en)

Spanish (es)

Inventor

Balasubramanian Gopalan

Laxmikant Atmaram Gharat

Neelima Khairatkar-Joshi

Original Assignee

Glenmark Pharmaceuticals Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-12-17

Filing date

2005-12-15

Publication date

2007-09-07

2005-12-15 Application filed by Glenmark Pharmaceuticals Sa filed Critical Glenmark Pharmaceuticals Sa

2007-09-07 Publication of MX2007007345A publication Critical patent/MX2007007345A/es

Links

150000002391 heterocyclic compounds Chemical class 0.000 title claims description 57
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230000000172 allergic effect Effects 0.000 title abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 45
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208000024780 Urticaria Diseases 0.000 claims abstract description 6
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206010006451 bronchitis Diseases 0.000 claims abstract description 6
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150000001408 amides Chemical class 0.000 claims description 11
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
210000000056 organ Anatomy 0.000 claims description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
125000000524 functional group Chemical group 0.000 claims description 9
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
206010061218 Inflammation Diseases 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
230000004054 inflammatory process Effects 0.000 claims description 8
210000004072 lung Anatomy 0.000 claims description 8
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239000011734 sodium Substances 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
HCUARRIEZVDMPT-UHFFFAOYSA-M 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)[O-])=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-M 0.000 claims description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
201000004624 Dermatitis Diseases 0.000 claims description 5
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
150000002357 guanidines Chemical class 0.000 claims description 5
201000006417 multiple sclerosis Diseases 0.000 claims description 5
LVJOLFKUHRCWKJ-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-(difluoromethoxy)-[1]benzofuro[2,3-d]pyridazine-9-carboxamide Chemical compound C1=2C3=CN=NC=C3OC=2C(OC(F)F)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl LVJOLFKUHRCWKJ-UHFFFAOYSA-N 0.000 claims description 5
JUOHGXWUIGXYHW-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-methoxy-[1]benzofuro[2,3-d]pyridazine-9-carboxamide Chemical compound C1=2C3=CN=NC=C3OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl JUOHGXWUIGXYHW-UHFFFAOYSA-N 0.000 claims description 5
201000008482 osteoarthritis Diseases 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
201000005539 vernal conjunctivitis Diseases 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000000044 Amnesia Diseases 0.000 claims description 4
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208000004756 Respiratory Insufficiency Diseases 0.000 claims description 4
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229910052731 fluorine Inorganic materials 0.000 claims description 4
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238000007254 oxidation reaction Methods 0.000 claims description 4
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125000004950 trifluoroalkyl group Chemical group 0.000 claims description 4
PZLSGUCLHNPDKP-UHFFFAOYSA-N 2-ethoxycarbonyl-7-methoxy-3-methyl-1-benzofuran-4-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C)=C(C(=O)OCC)OC2=C1OC PZLSGUCLHNPDKP-UHFFFAOYSA-N 0.000 claims description 3
GYRWJIZAUPBYTH-UHFFFAOYSA-N 6-(difluoromethoxy)-[1]benzofuro[3,2-c]pyridine-9-carboxylic acid Chemical compound O1C2=CC=NC=C2C2=C1C(OC(F)F)=CC=C2C(=O)O GYRWJIZAUPBYTH-UHFFFAOYSA-N 0.000 claims description 3
QWOQUANZBGCZSR-UHFFFAOYSA-N 6-methoxy-[1]benzofuro[2,3-d]pyridazine-9-carboxylic acid Chemical compound C12=CN=NC=C2OC2=C1C(C(O)=O)=CC=C2OC QWOQUANZBGCZSR-UHFFFAOYSA-N 0.000 claims description 3
IMTAMGSIJJNXET-UHFFFAOYSA-N 6-methoxy-[1]benzofuro[3,2-d]pyrimidine-9-carboxylic acid Chemical compound O1C2=CN=CN=C2C2=C1C(OC)=CC=C2C(O)=O IMTAMGSIJJNXET-UHFFFAOYSA-N 0.000 claims description 3
HGHMCNGBTJOMCM-UHFFFAOYSA-N 7-cyclopentyloxy-2-methyl-1-benzofuran-4-carbaldehyde Chemical compound C=12OC(C)=CC2=C(C=O)C=CC=1OC1CCCC1 HGHMCNGBTJOMCM-UHFFFAOYSA-N 0.000 claims description 3
DPAYSHNIQOADKU-UHFFFAOYSA-N 7-cyclopentyloxy-2-methyl-1-benzofuran-4-carboxylic acid Chemical compound C=12OC(C)=CC2=C(C(O)=O)C=CC=1OC1CCCC1 DPAYSHNIQOADKU-UHFFFAOYSA-N 0.000 claims description 3
XXXPYUMNOJLCQC-UHFFFAOYSA-N 7-hydroxy-2-methyl-1-benzofuran-4-carbaldehyde Chemical compound C1=CC(O)=C2OC(C)=CC2=C1C=O XXXPYUMNOJLCQC-UHFFFAOYSA-N 0.000 claims description 3
208000031091 Amnestic disease Diseases 0.000 claims description 3
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CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
229910004679 ONO2 Inorganic materials 0.000 claims description 3
230000006986 amnesia Effects 0.000 claims description 3
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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YAWXWFNFKRPNPG-UHFFFAOYSA-N methyl 6-(difluoromethoxy)-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC=C2C2=C1C(OC(F)F)=CC=C2C(=O)OC YAWXWFNFKRPNPG-UHFFFAOYSA-N 0.000 claims description 3
MYEPUBYGEHUKAM-UHFFFAOYSA-N methyl 8-methoxy-9-methyl-1-oxo-3,4-dihydro-2h-pyrido[3,4-b]indole-5-carboxylate Chemical compound C1=2C(C(=O)OC)=CC=C(OC)C=2N(C)C2=C1CCNC2=O MYEPUBYGEHUKAM-UHFFFAOYSA-N 0.000 claims description 3
ZKHQSQYLKSSYIP-UHFFFAOYSA-N methyl furan-3-carboxylate Chemical compound COC(=O)C=1C=COC=1 ZKHQSQYLKSSYIP-UHFFFAOYSA-N 0.000 claims description 3
NZAJCVXXUVCFAY-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-(difluoromethoxy)-[1]benzofuro[3,2-c]pyridine-9-carboxamide Chemical compound C1=2C3=CN=CC=C3OC=2C(OC(F)F)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl NZAJCVXXUVCFAY-UHFFFAOYSA-N 0.000 claims description 3
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RIIAHEIBOHZBED-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC2=C1SC=C2 RIIAHEIBOHZBED-UHFFFAOYSA-N 0.000 claims description 3
KSWHJNNNYBSXOI-UHFFFAOYSA-N (4-nitrophenyl) 6-(difluoromethoxy)-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)C1=CC=C(OC(F)F)C2=C1C1=CN=CC=C1O2 KSWHJNNNYBSXOI-UHFFFAOYSA-N 0.000 claims description 2
ACCWZPLSQUGKSH-UHFFFAOYSA-N (4-nitrophenyl) 6-methoxy-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC=C2C2=C1C(OC)=CC=C2C(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACCWZPLSQUGKSH-UHFFFAOYSA-N 0.000 claims description 2
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WWTRGZOOZOXQPJ-UHFFFAOYSA-N 2-o-tert-butyl 9-o-(4-nitrophenyl) 6-methoxy-3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridine-2,9-dicarboxylate Chemical compound C1=2C=3CN(C(=O)OC(C)(C)C)CCC=3OC=2C(OC)=CC=C1C(=O)OC1=CC=C([N+]([O-])=O)C=C1 WWTRGZOOZOXQPJ-UHFFFAOYSA-N 0.000 claims description 2
QRTKSZIHAVWBQR-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylic acid Chemical compound C1=2C(C(=O)O)=CC=C(OC(F)F)C=2OC(C2=O)=C1C=NN2C1=CC=C(Cl)C=C1 QRTKSZIHAVWBQR-UHFFFAOYSA-N 0.000 claims description 2
CUTMZWBUNGGDST-UHFFFAOYSA-N 4-chloro-6-methoxy-[1]benzofuro[3,2-d]pyrimidine Chemical compound O1C2=C(Cl)N=CN=C2C2=C1C(OC)=CC=C2 CUTMZWBUNGGDST-UHFFFAOYSA-N 0.000 claims description 2
KPRMKWDXGLPXIR-UHFFFAOYSA-N 6-methoxy-1h-[1]benzofuro[3,2-d]pyrimidin-4-one Chemical compound N1=CNC(=O)C2=C1C(C=CC=C1OC)=C1O2 KPRMKWDXGLPXIR-UHFFFAOYSA-N 0.000 claims description 2
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IWYBHOOJCQFRCR-UHFFFAOYSA-N 6-methoxy-[1]benzofuro[3,2-d]pyrimidine Chemical compound O1C2=CN=CN=C2C2=C1C(OC)=CC=C2 IWYBHOOJCQFRCR-UHFFFAOYSA-N 0.000 claims description 2
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ZXYGBDIEBIBVMM-UHFFFAOYSA-N CCOC(=O)C1C(=C2C(=C(C=CC2(C)C(=O)O)OC)O1)CBr Chemical compound CCOC(=O)C1C(=C2C(=C(C=CC2(C)C(=O)O)OC)O1)CBr ZXYGBDIEBIBVMM-UHFFFAOYSA-N 0.000 claims description 2
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AQACOZWSZCZEMD-UHFFFAOYSA-N [1]benzofuro[2,3-c]pyridine-5-carboxylic acid Chemical compound C1=NC=CC2=C1OC=1C2=C(C=CC=1)C(=O)O AQACOZWSZCZEMD-UHFFFAOYSA-N 0.000 claims description 2
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238000007256 debromination reaction Methods 0.000 claims description 2
WWAFCZXRNDQDHL-UHFFFAOYSA-N ethyl 5-[(3,5-dichloropyridin-4-yl)carbamoyl]-8-methoxy-3,4-dihydro-1h-[1]benzofuro[2,3-c]pyridine-2-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=23)=C1OC3=C(OC)C=CC=2C(=O)NC1=C(Cl)C=NC=C1Cl WWAFCZXRNDQDHL-UHFFFAOYSA-N 0.000 claims description 2
PMJRJLBAPXIOKR-UHFFFAOYSA-N ethyl 6-methoxy-3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridine-2-carboxylate Chemical compound O1C2=C(OC)C=CC=C2C2=C1CCN(C(=O)OCC)C2 PMJRJLBAPXIOKR-UHFFFAOYSA-N 0.000 claims description 2
IDEWKXNUUFCNKC-UHFFFAOYSA-N ethyl 8-methoxy-3,4-dihydro-1h-[1]benzothiolo[2,3-c]pyridine-2-carboxylate Chemical compound S1C2=C(OC)C=CC=C2C2=C1CN(C(=O)OCC)CC2 IDEWKXNUUFCNKC-UHFFFAOYSA-N 0.000 claims description 2
VMZKEKCUORDEAK-UHFFFAOYSA-N ethyl 9-[(3,5-dichloropyridin-4-yl)carbamoyl]-8-methoxy-3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridine-2-carboxylate Chemical compound C=12C=3CN(C(=O)OCC)CCC=3OC2=CC=C(OC)C=1C(=O)NC1=C(Cl)C=NC=C1Cl VMZKEKCUORDEAK-UHFFFAOYSA-N 0.000 claims description 2
LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 claims description 2
KXMVIFLLEKHMRP-UHFFFAOYSA-N methyl 1-chloro-6-(difluoromethoxy)-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC(Cl)=C2C2=C1C(OC(F)F)=CC=C2C(=O)OC KXMVIFLLEKHMRP-UHFFFAOYSA-N 0.000 claims description 2
VSFFKLVHCRNMSZ-UHFFFAOYSA-N methyl 1-chloro-6-hydroxy-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC(Cl)=C2C2=C1C(O)=CC=C2C(=O)OC VSFFKLVHCRNMSZ-UHFFFAOYSA-N 0.000 claims description 2
BHBABKPTSDRVLE-UHFFFAOYSA-N methyl 2-(bromomethyl)-7-cyclopentyloxy-1-benzofuran-4-carboxylate Chemical compound C1=2OC(CBr)=CC=2C(C(=O)OC)=CC=C1OC1CCCC1 BHBABKPTSDRVLE-UHFFFAOYSA-N 0.000 claims description 2
JYEKGXMBMUVVSR-UHFFFAOYSA-N methyl 2-(bromomethyl)-7-methoxy-1-benzofuran-4-carboxylate Chemical compound COC(=O)C1=CC=C(OC)C2=C1C=C(CBr)O2 JYEKGXMBMUVVSR-UHFFFAOYSA-N 0.000 claims description 2
AMMYCWWFXKQDTE-UHFFFAOYSA-N methyl 2-formyl-7-methoxy-1-benzofuran-4-carboxylate Chemical compound COC(=O)C1=CC=C(OC)C2=C1C=C(C=O)O2 AMMYCWWFXKQDTE-UHFFFAOYSA-N 0.000 claims description 2
WXXKJCOMRDZOIC-UHFFFAOYSA-N methyl 7-cyclopentyloxy-2-formyl-1-benzofuran-4-carboxylate Chemical compound C1=2OC(C=O)=CC=2C(C(=O)OC)=CC=C1OC1CCCC1 WXXKJCOMRDZOIC-UHFFFAOYSA-N 0.000 claims description 2
DZVQCNHEYYKZFC-UHFFFAOYSA-N methyl 7-methoxy-2-methyl-1-benzofuran-4-carboxylate Chemical compound COC(=O)C1=CC=C(OC)C2=C1C=C(C)O2 DZVQCNHEYYKZFC-UHFFFAOYSA-N 0.000 claims description 2
RHTPWNRCHPSWCU-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-(difluoromethoxy)-3-ethyl-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxamide Chemical compound C1=CC(OC(F)F)=C2OC=3C(=O)N(CC)N=CC=3C2=C1C(=O)NC1=C(Cl)C=NC=C1Cl RHTPWNRCHPSWCU-UHFFFAOYSA-N 0.000 claims description 2
KMFZDPMQRUOANW-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-(difluoromethoxy)-[1]benzofuro[2,3-d]pyridazine-9-carboxamide;sodium Chemical compound [Na].C1=2C3=CN=NC=C3OC=2C(OC(F)F)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl KMFZDPMQRUOANW-UHFFFAOYSA-N 0.000 claims description 2
LPXCMCBLUHLREW-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-(difluoromethoxy)-[1]benzofuro[3,2-c]pyridine-9-carboxamide;sodium Chemical compound [Na].C1=2C3=CN=CC=C3OC=2C(OC(F)F)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl LPXCMCBLUHLREW-UHFFFAOYSA-N 0.000 claims description 2
INIOYSSEQIZPQB-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-methoxy-[1]benzofuro[3,2-d]pyrimidine-9-carboxamide Chemical group C1=2C3=NC=NC=C3OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl INIOYSSEQIZPQB-UHFFFAOYSA-N 0.000 claims description 2
229910003813 NRa Inorganic materials 0.000 claims 18
JOTDFEIYNHTJHZ-UHFFFAOYSA-N furan-2,4-dicarboxylic acid Chemical compound OC(=O)C1=COC(C(O)=O)=C1 JOTDFEIYNHTJHZ-UHFFFAOYSA-N 0.000 claims 3
RECKPDLJZUFEKT-UHFFFAOYSA-N 3-cyclopentyl-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylic acid Chemical compound C1=2C(C(=O)O)=CC=C(OC(F)F)C=2OC(C2=O)=C1C=NN2C1CCCC1 RECKPDLJZUFEKT-UHFFFAOYSA-N 0.000 claims 2
SBEQDSMEVDDQMA-UHFFFAOYSA-N [1]benzofuro[3,2-c]pyridine-9-carboxylic acid Chemical compound C1=NC=CC2=C1C1=C(O2)C=CC=C1C(=O)O SBEQDSMEVDDQMA-UHFFFAOYSA-N 0.000 claims 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
KUMNHXJZVUDLKN-UHFFFAOYSA-N (4-nitrophenyl) 3-butyl-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylate Chemical compound O=C1N(CCCC)N=CC(C=23)=C1OC3=C(OC(F)F)C=CC=2C(=O)OC1=CC=C([N+]([O-])=O)C=C1 KUMNHXJZVUDLKN-UHFFFAOYSA-N 0.000 claims 1
PNAQJTUINPJBQC-UHFFFAOYSA-N (4-nitrophenyl) 6-(difluoromethoxy)-3-ethyl-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylate Chemical compound O=C1N(CC)N=CC(C=23)=C1OC3=C(OC(F)F)C=CC=2C(=O)OC1=CC=C([N+]([O-])=O)C=C1 PNAQJTUINPJBQC-UHFFFAOYSA-N 0.000 claims 1
UONRIEVHDZSAIW-TWGQIWQCSA-N (z)-3-(7-cyclopentyloxy-4-methoxycarbonyl-1-benzofuran-2-yl)prop-2-enoic acid Chemical compound C1=2OC(\C=C/C(O)=O)=CC=2C(C(=O)OC)=CC=C1OC1CCCC1 UONRIEVHDZSAIW-TWGQIWQCSA-N 0.000 claims 1
DHWRZDFGCCSMOD-UTCJRWHESA-N (z)-3-(7-methoxy-4-methoxycarbonyl-1-benzofuran-2-yl)prop-2-enoic acid Chemical compound COC(=O)C1=CC=C(OC)C2=C1C=C(\C=C/C(O)=O)O2 DHWRZDFGCCSMOD-UTCJRWHESA-N 0.000 claims 1
RDBHXJWSFLYMJN-UHFFFAOYSA-N 3-butyl-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C=NN(C3=O)CCCC)=C3OC2=C1OC(F)F RDBHXJWSFLYMJN-UHFFFAOYSA-N 0.000 claims 1
IQDYDNYMTODQPD-UHFFFAOYSA-N 6-(difluoromethoxy)-3-ethyl-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C=NN(C3=O)CC)=C3OC2=C1OC(F)F IQDYDNYMTODQPD-UHFFFAOYSA-N 0.000 claims 1
LHZGJXWOXSMWGZ-UHFFFAOYSA-N 6-methoxy-1-methyl-3H-[1]benzofuro[2,3-d]pyridazin-4-one Chemical compound CC=1C2=C(C(NN=1)=O)OC1=C2C=CC=C1OC LHZGJXWOXSMWGZ-UHFFFAOYSA-N 0.000 claims 1
DKVPCIRLNPJLKO-UHFFFAOYSA-N 6-methoxy-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridine-9-carboxylic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C(C(C(O)=O)=CC=C1OC)=C1O2 DKVPCIRLNPJLKO-UHFFFAOYSA-N 0.000 claims 1
XSQFTULXNGBZRI-UHFFFAOYSA-N 6-methoxy-5-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indole-9-carboxylic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C(C(C(O)=O)=CC=C1OC)=C1N2C XSQFTULXNGBZRI-UHFFFAOYSA-N 0.000 claims 1
HZLJCBXNXKYRCH-UHFFFAOYSA-N 6-methoxy-9-methyl-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-9-carboxylic acid Chemical compound N1C2CCN(C(=O)OC(C)(C)C)CC2=C2C1=C(OC)C=CC2(C)C(O)=O HZLJCBXNXKYRCH-UHFFFAOYSA-N 0.000 claims 1
NYUTUOKOZYMJIF-UHFFFAOYSA-N CC1=C2C(=C(N=N1)Cl)OC1=C2C=CC=C1OC Chemical compound CC1=C2C(=C(N=N1)Cl)OC1=C2C=CC=C1OC NYUTUOKOZYMJIF-UHFFFAOYSA-N 0.000 claims 1
XLVRNPOJNREXJT-UHFFFAOYSA-N CC1=C2C(=CN=N1)OC1=C2C=CC=C1OC Chemical compound CC1=C2C(=CN=N1)OC1=C2C=CC=C1OC XLVRNPOJNREXJT-UHFFFAOYSA-N 0.000 claims 1
102100040247 Tumor necrosis factor Human genes 0.000 claims 1
USQJUMKNJWUXHW-UHFFFAOYSA-N [1]benzofuro[3,2-c]pyridine Chemical compound C1=NC=C2C3=CC=CC=C3OC2=C1 USQJUMKNJWUXHW-UHFFFAOYSA-N 0.000 claims 1
LTVLBTUMIKLCEN-UHFFFAOYSA-N butyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCCCC)=CC2=C1 LTVLBTUMIKLCEN-UHFFFAOYSA-N 0.000 claims 1
125000002843 carboxylic acid group Chemical group 0.000 claims 1
IDSOLUXSVPUWAR-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylate Chemical compound C1=2C(C(=O)OCC)=CC=C(OC(F)F)C=2OC(C2=O)=C1C=NN2C1=CC=C(Cl)C=C1 IDSOLUXSVPUWAR-UHFFFAOYSA-N 0.000 claims 1
GMNAHXUPODXCMZ-UHFFFAOYSA-N ethyl 3-butyl-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylate Chemical compound C1=CC(C(=O)OCC)=C2C(C=NN(C3=O)CCCC)=C3OC2=C1OC(F)F GMNAHXUPODXCMZ-UHFFFAOYSA-N 0.000 claims 1
KZHSBLYJYQJJMY-UHFFFAOYSA-N ethyl 3-cyclopentyl-6-(difluoromethoxy)-4-oxo-[1]benzofuro[2,3-d]pyridazine-9-carboxylate Chemical compound C1=2C(C(=O)OCC)=CC=C(OC(F)F)C=2OC(C2=O)=C1C=NN2C1CCCC1 KZHSBLYJYQJJMY-UHFFFAOYSA-N 0.000 claims 1
KHNOEKPAJYAEGM-UHFFFAOYSA-N ethyl 5-formyl-8-methoxy-3,4-dihydro-1h-[1]benzothiolo[2,3-c]pyridine-2-carboxylate Chemical compound S1C2=C(OC)C=CC(C=O)=C2C2=C1CN(C(=O)OCC)CC2 KHNOEKPAJYAEGM-UHFFFAOYSA-N 0.000 claims 1
FTQDASPHTQWODM-UHFFFAOYSA-N ethyl 9-formyl-6-methoxy-3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridine-2-carboxylate Chemical compound O1C2=C(OC)C=CC(C=O)=C2C2=C1CCN(C(=O)OCC)C2 FTQDASPHTQWODM-UHFFFAOYSA-N 0.000 claims 1
BDBWMKJQRNCCNU-UHFFFAOYSA-N methyl 1-chloro-6-methoxy-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC(Cl)=C2C2=C1C(OC)=CC=C2C(=O)OC BDBWMKJQRNCCNU-UHFFFAOYSA-N 0.000 claims 1
QQRXTKRNACQOAE-UHFFFAOYSA-N methyl 4-methoxy-3-[2-(1-methyl-2-oxopiperidin-3-ylidene)hydrazinyl]benzoate Chemical compound COC(=O)C1=CC=C(OC)C(NN=C2C(N(C)CCC2)=O)=C1 QQRXTKRNACQOAE-UHFFFAOYSA-N 0.000 claims 1
OTPPOGWRINGOKF-UHFFFAOYSA-N methyl 6-cyclopentyloxy-1-oxo-2h-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound C1=2OC3=CC=NC(O)=C3C=2C(C(=O)OC)=CC=C1OC1CCCC1 OTPPOGWRINGOKF-UHFFFAOYSA-N 0.000 claims 1
ZOUTZVLMUQGAKH-UHFFFAOYSA-N methyl 6-methoxy-1-oxo-2h-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC(O)=C2C2=C1C(OC)=CC=C2C(=O)OC ZOUTZVLMUQGAKH-UHFFFAOYSA-N 0.000 claims 1
MXGHMYKSDZDECI-UHFFFAOYSA-N methyl 6-methoxy-[1]benzofuro[3,2-c]pyridine-9-carboxylate Chemical compound O1C2=CC=NC=C2C2=C1C(OC)=CC=C2C(=O)OC MXGHMYKSDZDECI-UHFFFAOYSA-N 0.000 claims 1
PLSFVWNFJPRHHP-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-methoxy-1,2,3,4-tetrahydro-[1]benzofuro[3,2-c]pyridine-9-carboxamide;hydrochloride Chemical compound Cl.C1=2C=3CNCCC=3OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl PLSFVWNFJPRHHP-UHFFFAOYSA-N 0.000 claims 1
BFHCQDAEGZXGMQ-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-6-methoxy-[1]benzofuro[3,2-c]pyridine-9-carboxamide Chemical compound C1=2C3=CN=CC=C3OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl BFHCQDAEGZXGMQ-UHFFFAOYSA-N 0.000 claims 1
RGODBZXDBWSNNS-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-8-methoxy-1,2,3,4-tetrahydro-[1]benzofuro[2,3-c]pyridine-5-carboxamide;hydrochloride Chemical compound Cl.C1=2C=3CCNCC=3OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl RGODBZXDBWSNNS-UHFFFAOYSA-N 0.000 claims 1
APKBNIQVILDYRI-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-8-methoxy-1,2,3,4-tetrahydro-[1]benzothiolo[2,3-c]pyridine-5-carboxamide;hydrochloride Chemical compound Cl.C1=2C=3CCNCC=3SC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl APKBNIQVILDYRI-UHFFFAOYSA-N 0.000 claims 1
QZRSYEPEXBZCBO-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-8-methoxy-2,9-dimethyl-1-oxo-3,4-dihydropyrido[3,4-b]indole-5-carboxamide Chemical compound C1=2C=3CCN(C)C(=O)C=3N(C)C=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl QZRSYEPEXBZCBO-UHFFFAOYSA-N 0.000 claims 1
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Classifications

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MX2007007345A 2004-12-17 2005-12-15 Compuestos heterociclicos novedosos utiles para el tratamiento de trastornos inflamatorios y alergicos. MX2007007345A (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US63723204P	2004-12-17	2004-12-17
IN1352MU2004		2004-12-17
PCT/IB2005/003798 WO2006064355A2 (fr)	2004-12-17	2005-12-15	Nouveaux composes heterocycliques utiles pour le traitement de troubles inflammatoires et allergiques

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MX2007007345A true MX2007007345A (es)	2007-09-07

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Application Number	Title	Priority Date	Filing Date
MX2007007345A MX2007007345A (es)	2004-12-17	2005-12-15	Compuestos heterociclicos novedosos utiles para el tratamiento de trastornos inflamatorios y alergicos.

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Country	Link
US (1)	US8129401B2 (fr)
EP (1)	EP1831227B1 (fr)
JP (1)	JP5122974B2 (fr)
KR (1)	KR101317119B1 (fr)
AP (1)	AP2334A (fr)
AR (1)	AR066386A1 (fr)
AU (1)	AU2005315319B2 (fr)
BR (1)	BRPI0517211B8 (fr)
CA (1)	CA2591438C (fr)
EA (1)	EA014956B1 (fr)
IL (1)	IL183827A (fr)
MA (1)	MA29231B1 (fr)
MX (1)	MX2007007345A (fr)
MY (1)	MY143483A (fr)
NZ (1)	NZ555809A (fr)
PL (1)	PL1831227T3 (fr)
TW (1)	TWI359814B (fr)
WO (1)	WO2006064355A2 (fr)

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2005
- 2005-12-15 BR BRPI0517211A patent/BRPI0517211B8/pt not_active IP Right Cessation
- 2005-12-15 CA CA2591438A patent/CA2591438C/fr not_active Expired - Lifetime
- 2005-12-15 AU AU2005315319A patent/AU2005315319B2/en not_active Ceased
- 2005-12-15 EA EA200701268A patent/EA014956B1/ru not_active IP Right Cessation
- 2005-12-15 EP EP05826587.7A patent/EP1831227B1/fr not_active Expired - Lifetime
- 2005-12-15 AP AP2007004031A patent/AP2334A/xx active
- 2005-12-15 KR KR1020077014219A patent/KR101317119B1/ko not_active Expired - Fee Related
- 2005-12-15 PL PL05826587T patent/PL1831227T3/pl unknown
- 2005-12-15 MX MX2007007345A patent/MX2007007345A/es active IP Right Grant
- 2005-12-15 NZ NZ555809A patent/NZ555809A/en not_active IP Right Cessation
- 2005-12-15 AR ARP050105281A patent/AR066386A1/es unknown
- 2005-12-15 JP JP2007546221A patent/JP5122974B2/ja not_active Expired - Fee Related
- 2005-12-15 WO PCT/IB2005/003798 patent/WO2006064355A2/fr not_active Ceased
- 2005-12-16 TW TW094144699A patent/TWI359814B/zh not_active IP Right Cessation
- 2005-12-16 MY MYPI20055953A patent/MY143483A/en unknown
2007
- 2007-06-10 IL IL183827A patent/IL183827A/en not_active IP Right Cessation
- 2007-07-12 MA MA30075A patent/MA29231B1/fr unknown
2011
- 2011-04-15 US US13/087,826 patent/US8129401B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
BRPI0517211A (pt)	2008-09-30
KR101317119B1 (ko)	2013-10-11
AP2334A (en)	2011-12-06
PL1831227T3 (pl)	2013-10-31
US8129401B2 (en)	2012-03-06
AP2007004031A0 (en)	2007-06-30
AR066386A1 (es)	2009-08-19
IL183827A (en)	2013-02-28
TW200634015A (en)	2006-10-01
JP2008524201A (ja)	2008-07-10
CA2591438C (fr)	2014-04-29
AU2005315319A1 (en)	2006-06-22
EA200701268A1 (ru)	2007-12-28
BRPI0517211B8 (pt)	2021-05-25
KR20070100254A (ko)	2007-10-10
JP5122974B2 (ja)	2013-01-16
CA2591438A1 (fr)	2006-06-22
MA29231B1 (fr)	2008-02-01
IL183827A0 (en)	2007-09-20
NZ555809A (en)	2010-07-30
WO2006064355A2 (fr)	2006-06-22
EP1831227A2 (fr)	2007-09-12
EP1831227B1 (fr)	2013-06-19
WO2006064355A3 (fr)	2006-08-03
AU2005315319B2 (en)	2011-07-07
BRPI0517211B1 (pt)	2020-08-11
US20110190303A1 (en)	2011-08-04
HK1111147A1 (en)	2008-08-01
MY143483A (en)	2011-05-31
TWI359814B (en)	2012-03-11
EA014956B1 (ru)	2011-04-29

Legal Events

Date	Code	Title	Description
2012-03-22	FG	Grant or registration

Publication	Publication Date	Title
MX2007007345A (es)	2007-09-07	Compuestos heterociclicos novedosos utiles para el tratamiento de trastornos inflamatorios y alergicos.
AU2003269317B2 (en)	2009-10-29	Novel tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
JP5111491B2 (ja)	2013-01-09	ピロロ−およびピラゾロ−ピリミジン化合物、およびそれらの使用方法
CA3210332A1 (fr)	2022-08-11	Inhibiteurs de prmt5 tricycliques-amido-bicycliques
AU2004228453A1 (en)	2004-10-21	Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
MXPA05004670A (es)	2005-08-18	Agentes anti-infecciones.
ZA200706097B (en)	2008-07-30	Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders
TW201014855A (en)	2010-04-16	Compounds for the treatment of hepatitis C
CN101679272B (zh)	2013-02-06	作为腺苷a3受体配体的三唑并[1,5-a]喹啉类
CN111606928A (zh)	2020-09-01	一种氮杂环二酮化合物及其制备方法
WO2004069831A1 (fr)	2004-08-19	Composes tricycliques utiles dans le traitement de troubles inflammatoires et allergiques, et procede de preparation de ces composes
AU2006273692A1 (en)	2007-02-01	1,4-Dihydropyridine-fused heterocycles, process for preparing the same, use and compositions containing them
WO2003103666A2 (fr)	2003-12-18	Nouvelles 4,5-dihydro-imidazo[4,5,1-ij]quinolin-6-ones
HK1111147B (en)	2014-03-14	Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders
JPH11322748A (ja)	1999-11-24	複素環化合物、その製造法および用途
CN101263144A (zh)	2008-09-10	新颖的吡啶并[3′,2′:4,5]呋喃并[3,2－d]嘧啶衍生物
CN120230096A (zh)	2025-07-01	含哌啶多环类衍生物调节剂、其制备方法和应用
WO2006051390A1 (fr)	2006-05-18	Composes heterocycliques utilises pour le traitement de troubles inflammatoires et allergiques, compositions pharmaceutiques contenant ces composes et procedes permettant de les preparer
WO2006040650A1 (fr)	2006-04-20	Derives de 4-methoxyacridine-1-carboxamide et les analogues phenazine et oxanthrene utilises comme inhibiteurs pde4 pour le traitement de l'asthme et la maladie pulmonaire chronique (copd)
JP2008508347A (ja)	2008-03-21	５置換された１Ｈ−ピロロ［３，２−ｂ］ピリジン
TW200427678A (en)	2004-12-16	Anti-infective agents
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